Who is Alex Jacob?

Alex Jacob has over $2.6 million in lifetime tournament poker earnings, but his legacy will forever be linked a different game – trivia – and his memorable appearances on Jeopardy.

David Hill
May 18, 2023

The category was “Recent Bestsellers.” It was a Daily Double, and Alex Jacob bet it all. That was no surprise. Alex always bet it all. He didn’t get to the 2015 Jeopardy Tournament of Champions by playing defense. He had already accumulated $5,000. His closest opponent had $600. His other opponent had yet to answer a single question. That was also no surprise. The answer was “A noted children’s author, she hit the bestseller list in 2015 with ‘In the Unlikely Event,’ her first book for adults in 17 years.”

Alex said nothing for what seemed like an eternity. He shook his head from side to side. He imperceptibly shrugged his shoulders. Sweat beaded on his brow. After some time, Alex Trebek had to break the silence. He whispered “Alex?”

Alex Jacob looked defeated. Had he finally gotten too far over his skis? After winning $151,802 in seven straight appearances, and now breaking off a run in the Tournament of Champions, was this the question that would finally humble him?

“I didn’t know for sure,” Alex said, recounting that day. “There’s just like a certain set of answers that the show is likely to ask about. I guess you could think of it as a frequency graph in my head, where Judy Blume would probably be at the highest in terms of children’s authors.”

From there, Alex turned to context clues in the answer. It’s a woman, and given that her last book for adults was 17 years ago, she’s probably an older woman. “And I guess the two would be Judy Blume and Beverly Cleary. And I would probably give Judy Blume a slight edge, as to coming up a little more frequently, so I went with her.”

He closed his eyes and said “Who is Blume?” His whole body seemed to shrug as he said it, betraying his doubt. Alex Trebek answers with “You’re right,” and Alex Jacob exhaled. The audience, and even his opponents, applauded, so sure they were that he would miss it. But he didn’t miss it. Alex Jacob never misses.

Alex grew up in Parkland, Florida in the 1980s, and he says that even as a child he wanted to be a game show contestant. Jeopardy, The Price is Right, Press Your Luck – they held him in their thrall, and cemented his love of games. His parents, who gifted him an almanac every year for Christmas, helped with the trivia.”I would spend a lot of time reading through that. I always enjoyed knowing things. I wanted to pick up as many facts as I could.”

In high school he gravitated towards math, and participated in math competitions as a way to sate his passion for numbers and games. But eventually he found an even better way to mesh math and games, and make a little money for himself at the same time. Poker.

“The gambling age was 18 at the time and there were some casino boats that would go out for the night. And so I was a regular on those,” he said. “And at some point hosted my own game in, at my house for a little while with some local kids.”

If his parents were concerned about his new hobby, their fears were assuaged when he came home from a small tournament he won. It wasn’t the money that impressed them, which was about a thousand bucks. It was the hardware. “They had some absurdly large trophy that I brought home,” he said. His parents were impressed. “It was the biggest trophy I ever got, probably for anything I ever would [win].”

They didn’t need to worry about whether or not Alex’s head was screwed on straight enough to handle himself as a teenager on the casino boats. After all, he was accepted to Yale. After he graduated in 2002 he shipped off to New Haven to study math and economics. But poker was foremost on his mind. He quickly found the Trumbull College game, a home game at Yale that spawned players like Vanessa Selbst, who he played with regularly at stakes of $1-1 No Limit Hold’em.

While Alex was in college online poker took off, and he was able to put in serious work that also produced major results. “And suddenly I had the bankroll to just go play a $10k WPT tournament down the road if I want to.” Which is exactly what he did. He entered the 2005 $10,000 World Poker Finals at Foxwoods and finished 27th. A few months later he came back for the Foxwoods Poker Classic, and at the age of 21 finished second to Victor Ramdin for $655,507. “And then it was just kind of off to the races.”

By the end of that first year of playing live tournaments, Alex would add another million dollars to that $655,507.

At 21 years old, Alex Jacob won $655,507 for finishing second in the 2006 WPT Foxwoods Poker Classic.

He kept his winning streak going, living on the road, playing the circuit full time. “It was it was definitely a surreal thing, just kind of going stop to stop and kind of playing with all of the most famous poker players in the world.” But by 2010, poker had lost a lot of its luster for him. The road, the grind, the anxiety about poker’s uncertain future – he decided it wasn’t fun anymore.

“I mean, I guess it’s cliche to say it, but I was burned out.” So he joined the rat race. He got a job in Chicago as a currency trader, which afforded him time to climb down the rabbit hole of another passion – trivia.

Prior to moving to Chicago, Alex made Las Vegas his home, and every year the Trivia Championships of North America would be held there. He attended nearly every year. One year he noticed after hours a group of people had set up a simulated Jeopardy game. “I was riveted by that,” he says. “And eventually I found out that there was a community of people who played a version of that online. So I got involved with that.”

This online version of the simulated Jeopardy game was known as Vortex Jeopardy, though some jokingly called it “Fight Club,” because the rule was – you weren’t supposed to talk about it. It was strictly for those in the know. It was an underground training facility for trivia fanatics with one goal: to get on Jeopardy.

Vortex Jeopardy players played through actual episodes of the show or they could load up their own custom games. Alex found he loved to write his own clues and create his own games. But he also realized that was a great way for him to retain more information, by thinking through and designing his own categories and clues.

It wasn’t long before he could tell he was getting pretty good at it. “I felt at a certain point that I can probably pass the Jeopardy test and get on the show, but I wasn’t sure if I could really win. I didn’t think I was at the level yet, so I decided to wait to actually take the test. So I waited for several years.”

Alex was sure he was good enough to get on the show, something 100,000 people try to do every year, and only 460 of those get on the show. But if you get on the show and lose, you’re not getting that chance again, so Alex wanted to make sure that if he did get on, he’d win. The thing was, how would he know he was ready? Well, how did Mike McDermott know he was ready to roll up a stake and head to Las Vegas? By making a move on Johnny Chan, that’s how.

Alex played on Vortex Jeopardy for years, steadily getting better and better. He went from regularly getting stomped to regularly dominating games. Sometimes he would play with Roger Craig, 2011 Jeopardy Tournament of Champions winner. Eventually, he beat him. “I felt like, yeah, at that point that I was ready.”

Alex took the test in 2013 and made the cut to audition in person. His audition went well. He knew that to get on the show you needed to stand out, and he had grown his hair out into a large afro. He also used his trivia knowledge to make an impression. “I remember I impressed the contestant coordinator, Maggie, who’s like a legend at the show, because I knew the actor who played Marcus Welby MD. Robert Young, coincidentally, is the guy’s name.”

His name went into a pool of players, and he was told if they wanted him for a taping that they would call him within the next 18 months – but the phone never rang. “18 months came and went. And at that point I’d gotten the job in Chicago and was kind of embroiled in that, trying to do my best to do well at that.”

He thought his window had closed, and that he’d need to try out again. But then, after another two months had passed, Alex got the call. He was going to be on the show.

Alex was confident headed into his first game. “I felt like it was gonna be tough to put two people up there who were a favorite against me.” They did have a tough time, and he went on a tear, burning through twelve opponents with relative ease, including one of his Fight Club compatriots. He won six straight games. In four of those games, he went into Final Jeopardy with more than double his closest opponent, a “lock game,” and used Final Jeopardy to write messages to his friends and family. He saw nothing between him and Ken Jennings but daylight.

“The more that number increases like five-day champion, six-day champion, the more and more fear in your opponent’s hearts. Your edge over your opponent just grows and grows. And you’re getting more and more buzzer practice,” he says. “I just felt like I could see it. It wasn’t the kind of thing where I was, like, celebrating too early or anything. But I could just see getting to that point where I could coast and really just bust off a long run.”

In Alex’s seventh appearance on the show, at the end of the first round he was ahead with $9,400 to $2,800 and $2,600. Halfway through Double Jeopardy, Alex was ahead with $25,200, while Todd Lovell, one of his opponents, still had only $2,600. Todd then answered four questions in a row, got a Daily Double and bet it all and won, and they went into Final Jeopardy with Alex’s $26,400 to Todd’s $18,400. The category: Business. The answer: This social media company launched in October 2010; in 2012, with about a dozen employees and no revenue, it sold for $1 billion. Alex was blissfully off social media. He had no idea. The word Instagram never came to him, and he lost.

“I was gutted.”

Ironically, Alex says, it was his own fault. By building up such a commanding lead, he gave Todd no choice but to go all in when he found the Daily Double. Otherwise perhaps he’d have been more conservative. “He still had to have the guts to do it, so credit to him.”

His streak was good enough to earn him an entry into the Tournament of Champions for 2015, and Alex resolved to win it. “Maybe partly because I was cut short a little bit that I was extra hungry. Maybe I felt like I had something to prove or something like that. I don’t know. I just definitely was super focused on trying to win that tournament.”

His focus paid off. He won all four of his TOC rounds with “lock games,” and even defeated 13-time champion Matt Jackson. Afterwards Alex Trebek told him his performance in the finals was “the most dominant performance by anyone in any of our tournaments.”

Today, Alex Jacob continues to compete in trivia competitions, but has found that his real passion is in writing his own games. But instead of writing practice questions and games for himself to train for Jeopardy, he makes them for others. “I decided I wanted to make something that I wish existed when I was studying for Jeopardy. Just like a fun league that would also be focused on the type of content that comes up on Jeopardy and other quiz shows.”

What he designed is called School of Trivia, a substack that publishes every weekday with Alex’s writing on a trivia topic, then a five-question quiz on that topic at the end of the week. Subscribers then submit their answers and confidence scores and are scored against everyone else in the league. Alex does all the writing, scoring, and administering himself. But the work is worth it, because he not only enjoys writing and learning from the quiz and people’s answers, he also enjoys training his own army of Jeopardy warriors in his own next-generation vortex.

Nine of his subscribers were in the last Jeopardy Tournament of Champions. Two of his subscirbers, Andrew and Mattea, are on Jeopardy Masters this week. He also has subscribers who have appeared on and won game shows from Masterminds to People Puzzler. “I love to watch them do well. I’ve probably never fist pumped so hard than when watching some of these games.”

Alex doesn’t think you need to be a genius to do what he’s done. “People will say that I’m smart and I think they are saying that because I’m like a Jeopardy champion. And I kind of always bristle at that a little bit because it’s not really smart. It’s just, like, knowing facts. It’s not really the same thing as intelligence.” But if intelligence is the application of knowledge, Alex is clearly very intelligent. He’s been successful at everything that has ever piqued his curiosity, and remarkably so at that. He has found a way to make a stimulating life for himself, filling his days with things that he loves. And, for better or for worse given it ended his first run on Jeopardy, Alex finally signed up for Instagram.